RU2015119606A - LIQUID APPLICABLE WATERPROOFING ROOF MEMBRANE CONTAINING LONG CHAIN ALDIMINE - Google Patents

LIQUID APPLICABLE WATERPROOFING ROOF MEMBRANE CONTAINING LONG CHAIN ALDIMINE Download PDF

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RU2015119606A
RU2015119606A RU2015119606A RU2015119606A RU2015119606A RU 2015119606 A RU2015119606 A RU 2015119606A RU 2015119606 A RU2015119606 A RU 2015119606A RU 2015119606 A RU2015119606 A RU 2015119606A RU 2015119606 A RU2015119606 A RU 2015119606A
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aldimine
formula
membrane according
range
mol
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RU2015119606A
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Урс БУРКХАРД
Урсула ШТАДЕЛЬМАНН
Ганс ХЕБЕРЛЕ
Майкл БИРН
Марк ГАТРЕЛЛ
Александр КАУАРД
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Сикэ Текнолоджи Аг
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/08—Polyurethanes from polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/302—Water
    • C08G18/307—Atmospheric humidity
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3253—Polyamines being in latent form
    • C08G18/3256—Reaction products of polyamines with aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
    • E—FIXED CONSTRUCTIONS
    • E04—BUILDING
    • E04D—ROOF COVERINGS; SKY-LIGHTS; GUTTERS; ROOF-WORKING TOOLS
    • E04D7/00—Roof covering exclusively consisting of sealing masses applied in situ; Gravelling of flat roofs
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2190/00—Compositions for sealing or packing joints
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/10—Scrim [e.g., open net or mesh, gauze, loose or open weave or knit, etc.]

Claims (52)

1. Однокомпонентная отверждающаяся под действием влаги наносимая в жидком виде гидроизоляционная мембрана, содержащая1. A one-component moisture-curable liquid-applied waterproofing membrane containing по меньшей мере один полиуретановый полимер с изоцианатными функциональными группами; at least one polyurethane polymer with isocyanate functional groups; по меньшей мере один альдимин формулы (I) at least one aldimine of formula (I)
Figure 00000001
Figure 00000001
 где m равно 2 или 3,where m is 2 or 3, А представляет собой двухвалентный или трехвалентный гидрокарбильный фрагмент со средней молекулярной массой в диапазоне от 800 до 4000 г/моль, содержащий простые эфирные группы, иAnd represents a divalent or trivalent hydrocarbyl fragment with an average molecular weight in the range from 800 to 4000 g / mol, containing ether groups, and Z представляет собой одновалентный С3-С30 гидрокарбильный фрагмент, факультативно содержащий простую эфирную, карбонильную, сложноэфирную, амидную, уретановую, мочевинную или третичную аминную группы; иZ is a monovalent C 3 -C 30 hydrocarbyl moiety optionally containing an ether, carbonyl, ester, amide, urethane, urea or tertiary amine group; and по меньшей мере один отвердитель, который представляет собой оксазолидин или альдимин, отличный от альдимина формулы (I). at least one hardener, which is an oxazolidine or aldimine other than the aldimine of formula (I). 2. Мембрана по п. 1, отличающаяся тем, что А представляет собой двухвалентный или трехвалентный гидрокарбильный фрагмент со средней молекулярной массой в диапазоне от 1000 до 3000 г/моль, содержащий звенья оксиэтилена и/или звенья 1,2-оксипропилена.2. The membrane according to claim 1, characterized in that A is a divalent or trivalent hydrocarbyl fragment with an average molecular weight in the range from 1000 to 3000 g / mol, containing oxyethylene units and / or 1,2-hydroxypropylene units. 3. Мембрана по п. 1, отличающаяся тем, что альдимин формулы (I) представляет собой альдимин формулы (Iа)3. The membrane according to claim 1, characterized in that the aldimine of formula (I) is an aldimine of formula (Ia)
Figure 00000002
Figure 00000002
 где R1 и R2 представляют собой одинаковые или разные C1-С12 линейные или разветвленные алкилы, или вместе образуют двухвалентный линейный или разветвленный С4-С12 гидрокарбильный фрагмент, являющийся составной частью 5-8-членного карбоциклического кольца;where R 1 and R 2 are the same or different C 1 -C 12 linear or branched alkyls, or together form a divalent linear or branched C 4 -C 12 hydrocarbyl fragment, which is part of a 5-8 membered carbocyclic ring; R3 представляет собой водород или линейный или разветвленный C1-С12 алкил, арилалкил или алкоксикарбонил, иR 3 represents hydrogen or a linear or branched C 1 -C 12 alkyl, arylalkyl or alkoxycarbonyl, and X представляет собой одновалентный фрагмент формул
Figure 00000003
или
Figure 00000004
,X is a monovalent fragment of the formulas
Figure 00000003
or
Figure 00000004
, где R4 и R5 представляют собой одинаковые или разные линейные или разветвленные C1-С20 алкилы, циклоалкилы или аралкилы, факультативно содержащие простые эфирные группы, или вместе образуют двухвалентный линейный или разветвленный С4-С12 гидрокарбильный фрагмент, являющийся составной частью 5-8-членного гетероциклического кольца, которое, кроме атома азота, может содержать простую эфирную, простую тиоэфирную или третичную аминную группу, иwhere R 4 and R 5 are the same or different linear or branched C 1 -C 20 alkyls, cycloalkyls or aralkyls optionally containing ether groups, or together form a divalent linear or branched C 4 -C 12 hydrocarbyl moiety, which is part 5 An 8-membered heterocyclic ring, which, in addition to the nitrogen atom, may contain an ether, simple thioether or tertiary amine group, and R6 представляет собой водород или одновалентный С2-С20 гидрокарбильный фрагмент, факультативно содержащий простую эфирную, карбонильную или сложноэфирную группы.R 6 is hydrogen or a monovalent C 2 -C 20 hydrocarbyl moiety optionally containing an ether, carbonyl or ester group. 4. Мембрана по п. 1, отличающаяся тем, что альдимин формулы (I) выбран из группы, состоящей из N,N'-бис(2,2-диметил-3-(N-морфолино)пропилиден)полиоксипропилендиаминов со средней молекулярной массой в диапазоне от 1300 до 4400 г/моль, N,N'-бис(2,2-диметил-3-лауроилоксипропилиден)-полиоксипропиленди-аминов со средней молекулярной массой в диапазоне от 1500 до 4600 г/моль, N,N',Nʺ-трис(2,2-диметил-3-(N-морфолино)пропилиден)полиоксипропилентриаминов со средней молекулярной массой в диапазоне от 3000 до 4000 г/моль, N,N',Nʺ-трис(2,2-диметил-3-лауроилоксипропилиден)полиоксипропилентриаминов со средней молекулярной массой в диапазоне от 3300 до 4300 г/моль, N,N'-бис(2,2-диметил-3-(N-морфолино)пропилиден)полиоксиэтилен-полиоксипропилендиаминов со средней молекулярной массой в диапазоне от 2000 до 2600 г/моль и N,N'-бис(2,2-диметил-3-лауроилоксипропилиден)полиоксиэтиленполиоксипропилендиаминов со средней молекулярной массой в диапазоне от 2200 до 2900 г/моль.4. The membrane according to claim 1, characterized in that the aldimine of formula (I) is selected from the group consisting of N, N'-bis (2,2-dimethyl-3- (N-morpholino) propylidene) polyoxypropylene diamines with an average molecular weight in the range from 1300 to 4400 g / mol, N, N'-bis (2,2-dimethyl-3-lauroloxypropylidene) -polyoxypropylene diamines with an average molecular weight in the range from 1500 to 4600 g / mol, N, N ', Nʺ-tris (2,2-dimethyl-3- (N-morpholino) propylidene) polyoxypropylene triamines with an average molecular weight ranging from 3,000 to 4,000 g / mol, N, N ', Nʺ-tris (2,2-dimethyl-3 -lauroloxypropylidene) polyoxypropyl ntriamines with an average molecular weight in the range of 3300 to 4300 g / mol, N, N'-bis (2,2-dimethyl-3- (N-morpholino) propylidene) polyoxyethylene-polyoxypropylene diamines with an average molecular weight in the range of 2000 to 2600 g / mol and N, N'-bis (2,2-dimethyl-3-lauroloxypropylidene) polyoxyethylene polyoxypropylenediamine with an average molecular weight in the range from 2200 to 2900 g / mol. 5. Мембрана по п. 1, отличающаяся тем, что указанный по меньшей мере один отвердитель представляет собой альдимин формулы (III)5. The membrane according to claim 1, characterized in that said at least one hardener is an aldimine of the formula (III)
Figure 00000005
Figure 00000005
 где n равно 2 или 3,where n is 2 or 3, G представляет собой двухвалентный или трехвалентный гидрокарбильный фрагмент с молекулярной массой в диапазоне от 28 до 500 г/моль, факультативно содержащий простую эфирную или уретановую группы.G is a divalent or trivalent hydrocarbyl moiety with a molecular weight in the range of 28 to 500 g / mol, optionally containing ether or urethane groups. 6. Мембрана по п. 5, отличающаяся тем, что альдимин формулы (III) представляет собой альдимин формулы (IIIа)6. The membrane according to claim 5, characterized in that the aldimine of formula (III) is an aldimine of formula (IIIa)
Figure 00000006
.
Figure 00000006
. 7. Мембрана по любому из пп. 1-6, содержащая7. The membrane according to any one of paragraphs. 1-6 containing по меньшей мере один алифатический полиуретановый полимер с изоцианатными функциональными группами; at least one aliphatic polyurethane polymer with isocyanate functional groups; по меньшей мере один альдимин формулы (I); и at least one aldimine of formula (I); and по меньшей мере один альдимин формулы (IIIа), где X представляет собой N-морфолиновую группу. at least one aldimine of formula (IIIa), wherein X is an N-morpholine group. 8. Мембрана по любому из пп. 1-6, содержащая8. The membrane according to any one of paragraphs. 1-6 containing по меньшей мере один ароматический полиуретановый полимер с изоцианатными функциональными группами; at least one aromatic polyurethane polymer with isocyanate functional groups; по меньшей мере один альдимин формулы (I); и at least one aldimine of formula (I); and по меньшей мере один альдимин формулы (III), где Z представляет собой фенил. at least one aldimine of formula (III), wherein Z is phenyl. 9. Мембрана по любому из пп. 1-6, содержащая9. The membrane according to any one of paragraphs. 1-6 containing по меньшей мере один ароматический полиуретановый полимер с изоцианатными функциональными группами; at least one aromatic polyurethane polymer with isocyanate functional groups; по меньшей мере один альдимин формулы (I); и at least one aldimine of formula (I); and по меньшей мере один альдимин формулы (III а), где X представляет собой лауроилоксильную группу. at least one aldimine of formula (III a), wherein X is a lauroyloxyl group. 10. Мембрана по любому из пп. 1-6, отличающаяся тем, что отношение числа альдиминных групп из альдиминов формулы (I) к числу групп, активных по отношению к изоцианату, из оксазолидинов и альдиминов, отличных от альдиминов формулы (I), находится в диапазоне от 1/99 до 50/50.10. The membrane according to any one of paragraphs. 1-6, characterized in that the ratio of the number of aldimine groups from aldimines of formula (I) to the number of groups active with respect to isocyanate, from oxazolidines and aldimines other than aldimines of formula (I) is in the range from 1/99 to 50 /fifty. 11. Мембрана по любому из пп. 1-6, содержащая 100 г ЛОС на литр или менее.11. The membrane according to any one of paragraphs. 1-6, containing 100 g of VOCs per liter or less. 12. Применение мембраны по любому из пп. 1-11 для кровли.12. The use of the membrane according to any one of paragraphs. 1-11 for the roof. 13. Гидроизоляционная система, состоящая из13. Waterproofing system, consisting of факультативно праймера и/или грунтовки, optional primer and / or primer, одного или более слоев мембраны по любому из пп. 1-11, предпочтительно в комбинации с волокнистой армирующей сеткой, и one or more layers of the membrane according to any one of paragraphs. 1-11, preferably in combination with a fibrous reinforcing mesh, and факультативно отделочного покрытия. optional finish coating. 14. Способ гидроизоляции конструкции кровли, включающий14. A method of waterproofing a roof structure, including нанесение мембраны по любому из пп. 1-11, в жидком состоянии, на субстрат конструкции кровли, слоем толщиной в диапазоне от 0,5 до 3 мм; applying a membrane according to any one of paragraphs. 1-11, in a liquid state, on a substrate of a roof structure, with a layer thickness ranging from 0.5 to 3 mm; осуществление контакта мембраны с волокнистой армирующей сеткой в течение времени открытой выдержки мембраны; contacting the membrane with the fibrous reinforcing mesh during the open exposure time of the membrane; воздействие влаги на мембрану, для отверждения мембраны полностью или частично, с образованием эластичного покрытия, the action of moisture on the membrane to cure the membrane in whole or in part, with the formation of an elastic coating, факультативное нанесение второго слоя мембраны по любому из пп. 1-11 слоем толщиной в диапазоне от 0,5 до 3 мм и отверждения под воздействием влаги. optional application of the second layer of the membrane according to any one of paragraphs. 1-11 layer thickness in the range from 0.5 to 3 mm and curing under the influence of moisture. 15. Способ снижения вязкости однокомпонентной отверждающейся под действием влаги наносимой в жидком виде гидроизоляционной мембраны, содержащей по меньшей мере один полиуретановый полимер с изоцианатными функциональными группами, при помощи по меньшей мере одного альдимина формулы (I)15. A method of reducing the viscosity of a one-component moisture-curable, liquid-applied waterproofing membrane containing at least one polyurethane polymer with isocyanate functional groups, using at least one aldimine of the formula (I)
Figure 00000007
Figure 00000007
 где m равно 2 или 3,where m is 2 or 3, А представляет собой двухвалентный или трехвалентный гидрокарбильный фрагмент со средней молекулярной массой в диапазоне от 800 до 4000 г/моль, содержащий простые эфирные группы, иAnd represents a divalent or trivalent hydrocarbyl fragment with an average molecular weight in the range from 800 to 4000 g / mol, containing ether groups, and Z представляет собой одновалентный С3-С30 гидрокарбильный фрагмент, факультативно, содержащий простую эфирную, карбонильную, сложноэфирную, амидную, уретановую, мочевинную или третичную аминную группы.Z is a monovalent C 3 -C 30 hydrocarbyl moiety optionally containing an ether, carbonyl, ester, amide, urethane, urea or tertiary amine group.
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